Sodium Azide → HCID 178518972, compound

HRID 260893Notes

Reaction equation

HRID 260893 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[N-:5]=[N+:6]=[N-:7].[Na+].[Cl:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N:16]=[C:17]=[O:18].N([O-])=O.[Na+]>O.O1CCCC1>[CH:13]1[CH:12]=[C:11]([N:16]2[NH:7][N:6]=[N:5][C:17]2=[O:18])[C:10]([Cl:9])=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 33557Sodium AzideHCID 76833Chlorophenyl isocyanateHCID 6451240Aluminum(III) ChlorideHCID 23668193Sodium Nitrite

Product 1

HCID 178518972HCID 178518972, compoundYield 25.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Anhydrous aluminum chloride (1.5 g) was added to tetrahydrofuran (30 ml) with ice bath cooling and the resulting mixture was stirred for fifteen minutes. To the mixture was added sodium azide (0.65 g) and 2-chlorophenylisocyanate (1.53 g), followed by a sixteen hour-refluxing. After cooling, the reaction mixture was added with stirring to a mixture of sodium nitrite (1 g), water (200 ml) and ice (100 g) and the resulting mixture was worked up in the same way as in Comparative Synthesis Example 1 to obtain the desired 1-(2-chlorophenyl)-5(4H)-tetrazolinone (0.5 g) having a m.p. in the range of from 124.5° to 125.5° C. in a yield of 25% of theory.

Workup

  1. temperaturecooling
  2. waitfollowed by a sixteen hour
  3. temperature-refluxing
  4. temperatureAfter cooling
  5. additionthe reaction mixture was added
  6. customthe resulting mixture was worked up in the same way as in Comparative Synthesis Example 1

Sources & evidence

ORD record
ord-689c11898bfd4c73a8f35e5c0e15b267
Source dataset
uspto-grants-1996_06
Patent number
US05530135

Reaction notes

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